In 2001, The Learning Company, Inc. published The Oregon Trail: 5th Edition on Windows. This adventure and educational game is now considered abandonware as the license has expired and the developer has long since shut down operations.
This game unfortunately does not work on operating systems newer than Windows XP, because of the incompatible files found not in the game, but in the now defunct bundled "The Learning Company" launcher.
This version of the game has the launcher removed, and can be played by extracted the full game from the zipped folder. It works on all versions of Windows, including Windows 10 & Windows 11.
How to Install:
1- Download the ZIP file and extract the contents to C:\ You must extract to here only, or else it will crash. If you would rather install it somewhere else, you will have to open up the .ini file and change the install location path to the one you chose.
2-Open the folder, and double click the OTS.exe file, and you are good to go!
Drawbacks:
-The game may crash if you skip through the learning company icon loading at the beginning of startup, or during the first cutscene. In my experience this only happens once, and you can re-open the game and skip without issue. Don't ask me why it does this.
-The game will change your resolution to 640x480. This wouldn't be so bad, except that it doesn't change it back when you close it. You'll have to go into display settings and fix it yourself.
The little workarounds are annoying, but not a big deal considering you can still play this awesome game!
"I'm getting an error about not being able to find .dat file, and making sure the disc is in the CD-Rom"
Open the "Data" folder, and then right click the file named "Oregeon5.Dat". Click "Properties" from the menu that pops up, and then copy the file path listed under "Location" (to do this, right click the file path displayed, click "select all" and then right click again and click "copy",
Go back to the main game folder, and right click the file "OREGON5.INI" and click "open with" and select notepad. Then, underneath the section "[cdrom]" where it says "rsrcpath=" select the file path to the right of it, starting with "C" and then past in the file path you copied earlier. Save the file and close it.
After that, try starting the game. It should work this time. 👍